1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 178526468, compound

HRID 2414757Notes

Reaction equation

HRID 2414757 reaction equation
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.C(O[C:31](=[O:51])[CH:32]=[C:33]([NH:41][C:42]1[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=1)CCC>>[F:40][C:36]1[CH:35]=[C:34]([C:33]2[CH:32]=[C:31]([OH:51])[C:43]3[C:42](=[CH:47][CH:46]=[C:45]([N+:48]([O-:50])=[O:49])[CH:44]=3)[N:41]=2)[CH:39]=[CH:38][CH:37]=1

Participants

3

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 69202260HCID 69202260, compound

Product 1

HCID 178526468HCID 178526468, compoundYield 96%

Conditions

Temperature
250 °C

Procedure

Dowtherm A, 0.75 L, was placed in a 3 L three-neck flask, equipped with mechanical stirrer, Claisen adapter holding a thermocouple probe and reflux condenser with nitrogen inlet and heated to 250° C. To this was cautiously added in small portions 77.0 grams (0.215 moles) of 3-(4-nitrophenylamino)-3-(3-fluorophenyl)-acrylic acid butyl ester over the course of 0.25 hours. The mixture was maintained at 250° C. for 1.5 hours and then allowed to cool to 90° C. over the course of 2 hours. The mixture was treated with 1.0 L of hexanes, and allowed to cool to room temperature while string overnight. The tan solids were collected by suction filtration and washed with three 0.15 L portion of hexanes. The solids were dried under vacuum at 50° C. overnight to yield 58.63 grams (96.0%) of the title compound.

Workup

  1. customequipped with mechanical stirrer
  2. temperaturereflux condenser with nitrogen inlet
  3. temperatureThe mixture was maintained at 250° C. for 1.5 hours
  4. temperatureto cool to 90° C. over the course of 2 hours
  5. temperatureto cool to room temperature while string overnight
  6. filtrationThe tan solids were collected by suction filtration
  7. washwashed with three 0.15 L portion of hexanes
  8. customThe solids were dried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-ed7f957351104dd5ad4c79b573768617
Source dataset
uspto-grants-2004_11
Patent number
US06815447B2

Reaction notes

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